1) Furan and thiophene are 5-membered heterocyclic compounds containing oxygen and sulfur respectively. They are prepared via various synthetic routes and undergo electrophilic substitution and addition reactions.
2) Furan and thiophene have several medicinal uses. Furan derivatives like furosemide and ranitidine are used as diuretics and antiulcer drugs. Thiophene derivatives are used as antibiotics, antihistamines, anticonvulsants and anti-inflammatory drugs.
3) The document discusses the structures, properties, synthesis and reactions of furan and thiophene. It also outlines some of their common medicinal applications.
This slide discusses about basic indole nucleus, its chemistry, synthesis, reactions and medicinal uses of Indolyl derivatives..Indole is basically fused heterocyclic compound
This slide discusses about fused heterocyclic compound Acridine..the structural analogue of anthracene with one carbon group is replaced with nitrogen atom.
Unit iii heterocyclic compounds as per PCI Syllabus of POC-IIIGanesh Mote
Nomenclature of hetero cyclic compounds, classification of heterocyclic compounds, Reactivity, aromaticity, orbital picture, stability, resonance energy, resonance structure, basicity, method of preparation, reaction and medicinal uses of Pyrrole, furan and thiophene
B.phram
Semester .4
Subject : Organic chemistry - III
Use as reference and also usable for examination prearation.
gtu afflitited phramacy college's student may using this ppt.
This slides discusses about Isoquinoline nucleus (fused heterocyclic compound). this ring contain benzene ring fused with pyridine nucleus with nitrogen atom
Hetero-cyclic compounds unit III as per PCI syllabus for second year B pharmacy students.
It covers all the details regarding Furan, Pyrrole and Thiophene ring
This slide discusses about basic indole nucleus, its chemistry, synthesis, reactions and medicinal uses of Indolyl derivatives..Indole is basically fused heterocyclic compound
This slide discusses about fused heterocyclic compound Acridine..the structural analogue of anthracene with one carbon group is replaced with nitrogen atom.
Unit iii heterocyclic compounds as per PCI Syllabus of POC-IIIGanesh Mote
Nomenclature of hetero cyclic compounds, classification of heterocyclic compounds, Reactivity, aromaticity, orbital picture, stability, resonance energy, resonance structure, basicity, method of preparation, reaction and medicinal uses of Pyrrole, furan and thiophene
B.phram
Semester .4
Subject : Organic chemistry - III
Use as reference and also usable for examination prearation.
gtu afflitited phramacy college's student may using this ppt.
This slides discusses about Isoquinoline nucleus (fused heterocyclic compound). this ring contain benzene ring fused with pyridine nucleus with nitrogen atom
Hetero-cyclic compounds unit III as per PCI syllabus for second year B pharmacy students.
It covers all the details regarding Furan, Pyrrole and Thiophene ring
The class of organic compounds characterized by hydroxyl (-OH) group attached to an aromatic ring. Phenol is commonly known as carbolic acid. Phenols are aromatic components which contain one or more hydroxyl groups that are attached to an aromatic ring. Phenol is a benzene derivative and it consists of a phenyl bonded to a hydroxyl (-OH) group. General chemical formula of phenol is C6H5OH and molecular formula C6H6O.
Phenol is a monohydroxy derivative of benzene prepared by the replacing of one of the hydrogen of benzene by hydroxyl group. Phenol contain two part one part is aryl group (phenyl) and other is hydroxyl group.
On the basis of number of hydroxyl group bonded to benzene. It can be classified into di, tri, tetra hydroxyls benzene.
Phenols are organic compounds that contain a hydroxyl (-OH) group attached to an aromatic ring. The general formula for a phenol is ArOH, where Ar is an aromatic ring. The simplest example of a phenol is phenol itself, also known as carbolic acid.
Phenols are important compounds in organic chemistry and are used in a variety of industrial and biological applications. They are commonly used as disinfectants, antiseptics, and preservatives due to their antimicrobial properties. They are also used in the production of plastics, pharmaceuticals, and dyes.
Phenols are acidic compounds, meaning that they can donate a proton (H+) to a solvent or a base. This acidity is due to the stability of the phenoxide ion (ArO-), which is formed when a phenol loses a proton. The stability of the phenoxide ion is due to the resonance stabilization of the negative charge over the aromatic ring.
Phenols can undergo a variety of reactions, including electrophilic substitution, oxidation, and esterification. They can also be used as starting materials for the synthesis of more complex organic compounds.
Mitsunubu reaction had been synthesised by Japanese scientist OYO Mitsunbu.
It involves the Conversion of primary, Secondary alcohol into the ester group.
It follows SN2 mechanism.
PHENOL INTRODUCTION, REACTIVITY, ACIDITY, FACTOR AFFECTING ON ACIDITY, PREPARATION, REACTION,COMPARISON OF ACIDITY WITH ALCOHOL AND ACID, USES OF PHENOL, CRESOL, RESORCINOL, NAPTHOL
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The people of Punjab felt alienated from main stream due to denial of their just demands during a long democratic struggle since independence. As it happen all over the word, it led to militant struggle with great loss of lives of military, police and civilian personnel. Killing of Indira Gandhi and massacre of innocent Sikhs in Delhi and other India cities was also associated with this movement.
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The Roman Empire A Historical Colossus.pdfkaushalkr1407
The Roman Empire, a vast and enduring power, stands as one of history's most remarkable civilizations, leaving an indelible imprint on the world. It emerged from the Roman Republic, transitioning into an imperial powerhouse under the leadership of Augustus Caesar in 27 BCE. This transformation marked the beginning of an era defined by unprecedented territorial expansion, architectural marvels, and profound cultural influence.
The empire's roots lie in the city of Rome, founded, according to legend, by Romulus in 753 BCE. Over centuries, Rome evolved from a small settlement to a formidable republic, characterized by a complex political system with elected officials and checks on power. However, internal strife, class conflicts, and military ambitions paved the way for the end of the Republic. Julius Caesar’s dictatorship and subsequent assassination in 44 BCE created a power vacuum, leading to a civil war. Octavian, later Augustus, emerged victorious, heralding the Roman Empire’s birth.
Under Augustus, the empire experienced the Pax Romana, a 200-year period of relative peace and stability. Augustus reformed the military, established efficient administrative systems, and initiated grand construction projects. The empire's borders expanded, encompassing territories from Britain to Egypt and from Spain to the Euphrates. Roman legions, renowned for their discipline and engineering prowess, secured and maintained these vast territories, building roads, fortifications, and cities that facilitated control and integration.
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Roman architecture and engineering achievements were monumental. They perfected the arch, vault, and dome, constructing enduring structures like the Colosseum, Pantheon, and aqueducts. These engineering marvels not only showcased Roman ingenuity but also served practical purposes, from public entertainment to water supply.
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Synthetic fiber production is a fascinating and complex field that blends chemistry, engineering, and environmental science. By understanding these aspects, students can gain a comprehensive view of synthetic fiber production, its impact on society and the environment, and the potential for future innovations. Synthetic fibers play a crucial role in modern society, impacting various aspects of daily life, industry, and the environment. ynthetic fibers are integral to modern life, offering a range of benefits from cost-effectiveness and versatility to innovative applications and performance characteristics. While they pose environmental challenges, ongoing research and development aim to create more sustainable and eco-friendly alternatives. Understanding the importance of synthetic fibers helps in appreciating their role in the economy, industry, and daily life, while also emphasizing the need for sustainable practices and innovation.
3. FURAN
WHAT IS FURAN ?
Furan is an unsaturated five membered heterocyclic
compound consists of oxygen as heteroatom at 1st
position.
Its vapours produce a bright green colour when brought
in contact with a pine splint moistened with con. HCl.
Molecular formula: C4 H4 O
Furan occurs in wood- tar.
4. SYNTHESIS/ PREPARATION
1) From carbohydrates
Most important source of furan is furfural
Pentoses
Acid hydrolysis
O
CHO
Furfural
O
CHO O
Furfural Furan
+ CO
Pd/ C
200°C
5. 2) Paal-Knorr synthesis of furan
Acid catalysed dehydration of 1,4 dicarbonyl compounds gives
Furan derivatives
CH2
CH2
C
C
O O R1
R C
O
C
CH
CH
R1
R
H+
-H2O
6. 3) Fiest-Benary synthesis
Reaction of α-haloketones with β-ketoester in presence
of base (but not ammonia) gives furan derivatives.
C CH3
O
C
H
C
H3
Cl
+
C
H2
C
O CH3
COOC2H5
C
O
C
C
C
CH3
C
H3
C
H3
NaOH/Pyridine
-HCl
-2H2O
COOC2H5
7. 4) From Furfural
Oxidation of furfural with potassium dichromate to give furoic
acid and subsequent decarboxylation at 200-300 °C
O
CHO
Furfural
K2Cr2O7
O
COOH
Δ
Furoic acid
O
+ CO2
Furan
8. 5) Commercial method
Decarboxylation of furfural in steam in presence of silver oxide
catalyst gives Furan.
9. REACTIONS
1) ELECTROPHILIC SUBSTITUTION REACTION:
Furan undergoes electrophilic substitution reaction at 2nd position
C2 attack gives more resonance structures than C3
12. Formylation
VI) Gattermann Koch formylation
VII) Vilsmeyer formylation
O
Furan
CO
+
O
CHO
+
AlCl3/ CuCl
HCl
Formyl chloride
Furfural
DMF- Dimethyl formamide
N
C
H3
C
H3
CHO
O
POCl3
DMF
O
CHO
Furan Furfural
13. 2) Diels-alder reaction
Furan is the least aromatic of the five-membered ring heterocyclics and act
as a diene.
So it undergoes Diels-Alder reaction with maleic anhydride to form an
addition product. This addition occurs across C-2 and C-5.
Pyrrole and Thiophene do not give this reaction as they are more aromatic in
character.
O
+ O
O
O
O
O
O
O
Furan Maleic anhydride
(Diels-Alder adduct)
(diene) (dienophile)
15. MEDICINAL USES
1) Furosemide
Diuretic drug used to reduce extra fluid in the body (oedema) caused
by conditions such as heart failure, liver diseases and kidney disease.
This drug is also used to treat high blood pressure.
16. 2) Ranitidine
A H2 antagonist used to treat ulcers of the stomach and
intestines.
17. 3) Nitrofurantoin
An Antibiotic used for treating urinary tract infections caused by
bacteria.
20. THIOPHENE
WHAT IS THIOPHENE ?
Thiophene is an unsaturated five membered heterocyclic
compound consists of Sulphur as heteroatom at 1st
position.
Molecular formula: C4 H4 S
Thiophene occurs in coal- tar along with benzene
Due to its closeness of its boiling point (84 °C) with that of
benzene (80 °C), they can’t be separated by distillation.
Hence thiophene is always present as an impurity in
commercial benzene.
21. Indophenine test:
Presence of thiophene in benzene may be detected by the appearance of a
blue colour with isatin and conc. Sulphuric acid.
Separation of thiophene from benzene:
❖ By repeated extraction of mixture with concentrated sulphuric acid and
so forms thiophene-2-sulphonic acid which is soluble in sulphuric acid.
❖ Thiophene can also removed by refluxing the mixture with mercuric
acetate which mercurates thiophene easily.
❖ It can be regenerated from organomercury compound by heating with
hydrochloric acid.
❖ It can be removed from benzene by shaking with Raney Nickel.
22. SYNTHESIS
1) Paal knorr synthesis
The condensation of 1,4- dicarbonyl compounds with phosphorus
pentasulphide in presence of sulphuric acid gives thiophene derivatives.
CH2
CH2
C
C
O O R1
R
C
S
C
CH
CH
R1
R
CH2
CH2
C
C
O S R1
R
-H2O
P2S5
H2SO4
23. 2) Simmons-Smith synthesis
Reaction of α-oxoketene dithioacetals with diiodomethane in
presence of zinc and copper gives thiophene derivatives.
C
C
O
C
CH3
H5C6
SC2H5
H5C2S
C
S
C
H
CH
C
SC2H5
H5C6
CH2I2
Zn - Cu
reflux, 45 mts
24. 3) Hinsberg synthesis
The condensation of 1,2-dicarbonyl compounds with diethyl
thiodiacetate in presence of a strong base gives thiophene
derivatives.
O
O
Ph
Ph
+
S
O
O
OC2H5
H5C2O
-2H2O t - BuO-
K+
S
O
O
Ph
Ph
OC2H5
H5C2O
Benzil
25. 4) From sodium succinate
Laboratory synthesis consists of heating sodium succinate with
phosphorous trisulphide gives thiophene.
CH2 CH2
C C
O
O
ONa
NaO
P2S3
Δ
S
+ 2NaPO2S + S
Sodiumsuccinate Thiophene
26. 5) From n-butane (Commercial)
By reaction of sulphur with n-butane in the gas phase at
650 °C
+ 4S 600 °C
S
+ 3H2S
Butane
Thiophene
Sulphur
Hydrogen sulphide
C
H3
CH2
CH3
CH2
27. REACTIONS
1) ELECTROPHILIC SUBSTITUTION REACTION:
Thiophene undergoes electrophilic substitution reaction at 2nd position
C2 attack gives more resonance contributing structures than C3
31. 2) Reaction with organolithium
Thiophene reacts with n-butyllithium to yield 2-lithium thiophene
which further reacts with carbon dioxide to form thiophene-2-
carboxylic acid.
S
+ C4H9Li
S
Li
CO2
H3O+
S
COOH
Thiophene n-butyllithium 2-lithiumthiophene Thiophene-2-carboxylicacid
32. 3) Reduction
S
Na - NH3
S
S
+
2,3-dihydrothiophene 2,5-dihydrothiophene
H2 - Pd
S
Tetrahydrothiophene
H2 - Ni
CH2 CH2
CH3
C
H3
+ NiS
Butane
33. 4) Oxidation
Thiophene does not oxidised, but tetrahydrothiophene oxidised
to respective sulphone.
S S
O O
(O)
Tetrahydrothiophene
Sulphone
34. Medicinal uses
1) Cephalothin
New semisynthetic antibacterial agent structurally related to
Pencillins.
It is effective against penicillinase- producing staphylococci as well as
other gram-positive and gram-negative organisms.
35. 2) Suprofen
A Nonsteroidal anti-inflammatory drug (NSAID).
It reduces pain and inflammation in the eyes.
Used ophthalmically to prevent pupil constriction (reduced pupil
size) during eye surgery.
36. 3) Methapyrilene
It has strong sedative effects.
An antihistamine drug formerly used as a sleep-inducing drugs.
37. 4) Tiagabine
Antiepileptic drug, also called as anticonvulsant.
Used in combination with other medication to treat partial
seizure in adults and children.
